5-(bromomethyl)-2,2,7,8-tetramethyl-3,4-dihydro-2H-chromen-6-yl methyl ether | 784143-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-(bromomethyl)-2,2,7,8-tetramethyl-3,4-dihydro-2H-chromen-6-yl methyl ether
• 英文别名: 2-(6-methoxy-2,2,7,8-tetramethylchroman-5-yl)methyl bromide
• CAS: 784143-53-9
• 化学式: C₁₅H₂₁BrO₂
• 分子量: 313.235
• InChiKey: WCYVTSIZYVWBTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-(bromomethyl)-2,2,7,8-tetramethyl-3,4-dihydro-2H-chromen-6-yl methyl ether 在 吡啶 、 sodium tetrahydroborate 、 四丁基碘化铵 、 potassium carbonate 、 copper(l) chloride 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 N-[1-(6-Methoxy-2,2,7,8-tetramethyl-chroman-5-ylmethyl)-2,3-dihydro-1H-indol-6-yl]-methanesulfonamide
  参考文献：
  名称：

  Synthesis and biological evaluation of benzopyran analogues bearing class III antiarrhythmic pharmacophores

  摘要：

  We have synthesized a series of compounds combining the hydroxy-benzopyran ring of vitamin E with the methylsulfonylaminophenyl group of class III antiarrhythmic drugs, connected through tertiary amine moieties. Evaluation of the antiarrhythmic and antioxidant activity of the new compounds was carried out on isolated rat heart preparations using the non-recirculating Langendorff mode. The new analogues were present, at 10 mu M concentration, during ischemia and reperfusion. Selected compounds were further studied by a conventional microelectrode method in order to get insight into their cellular mode of action. The most active compound, N-[4-[2-[[2-(3,4-dihydro-6-hydroxy-2,2,7,8-tetramethyl-2H-1-benzopyran-5-yl)ethyl] methylamine]ethyl]phenyl]methanesulfonamide (19a), reduces premature beats, prolongs QT and QRS intervals during ischemia and reperfusion, and reduces MDA content, leading to a fast recovery of the heart. In addition, it exhibits moderate class III antiarrhythmic action. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.065
• 作为产物：
  描述：

  3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-benzopyran-5-carboxaldehyde 在 三溴化磷 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 5-(bromomethyl)-2,2,7,8-tetramethyl-3,4-dihydro-2H-chromen-6-yl methyl ether
  参考文献：
  名称：

  Synthesis of chroman analogues of lipoic acid and evaluation of their activity against reperfusion arrhythmias

  摘要：

  Novel hybrids of lipoic acid and trolox connected through triamine spacers as well as analogues in which the lipoic acid was attached at different positions of the chroman moiety of vitamin E through an amide bond, were synthesized and exhibited strong inhibition of the microsomal lipid peroxidation. Moreover, the new molecules, at 1 muM concentration, reduced reperfusion arrhythimas and MDA content on isolated rat heart preparations, with the 2- and 5-subtituted chromans possessing the better cardioprotective activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.012

文献信息

• Design and synthesis of novel neuroprotective 1,2-dithiolane/chroman hybrids
  作者：Maria Koufaki、Christina Kiziridi、Xanthippi Alexi、Michael N. Alexis

  DOI：10.1016/j.bmc.2009.07.010

  日期：2009.9.1

  Novel 1,2-dithiolane/chroman hybrids bearing heterocyclic rings such as 1,2,4- and 1,3,4-oxadiazole, 1,2,3-triazole and tetrazole were designed and synthesized. The neuroprotective activity of the new analogues was tested against oxidative stress-induced cell death of glutamate-challenged HT22 hippocampal neurons. Our results show that bioisosteric replacement of amide group in 2-position of the chroman moiety, by 1,3,4- oxadiazole did not affect activity. However, analogue 5 bearing the 1,2,4- oxadiazole moiety showed improved neuroprotective activity. The presence of nitrogen heterocycles strongly influences the neuroprotective activity of 5-substituted chroman derivatives, depending on the nature of heterocycle. Replacement of the amide group of the first generation analogues by 1,2,4- oxadiazole or 1,2,3-triazole resulted in significant improvement of the activity against glutamate induced oxidative stress. (C) 2009 Elsevier Ltd. All rights reserved.